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Microparticle Preparation by a Propylene Carbonate Emulsification

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Microparticle Preparation by a Propylene Carbonate Emulsification International Journal of Pharmaceutics 544 (2018) 213–221 Contents lists available at ScienceDirect International Journal of Pharmaceutics journal homepage: www.elsevier.com/locate/ijpharm Microparticle preparation by a propylene carbonate emulsification- T extraction method ⁎ Daris Grizića, , Alf Lamprechta,b a Department of Pharmaceutics, Institute of Pharmacy, University of Bonn, Gerhard-Domagk-Str. 3, 53121 Bonn, Germany b PEPITE (EA4267), University of Burgundy/Franche-Comté, Besançon, France ARTICLE INFO ABSTRACT Keywords: The use of various harmful organic solvents for microparticle formulations is still widespread. Here, an alter- Propylene carbonate native low toxicity solvent (propylene carbonate; PC) is proposed for the preparation of poly(lactic-co-glycolic- PLGA acid) (PLGA) microparticles. Based on the classical emulsification-solvent extraction methodology, the use of PC Enhanced solvent extraction offers the unique advantage of an additional solvent extraction step using hydrolytic solvent cleavage during Microparticles microparticle preparation. Spherical, rough-surfaced microparticles were obtained with a volume median dia- meter range from 20 to 60 µm. The residual PC content has been identified to be the major factor for the solidification hindrance, leading to polymeric Tg shifting due to a plasticizing effect. When applying the en- hanced PC extraction step, the residual PC content was lowered from 8.8% to 2.7% and subsequently Tg values shifted from 8.2 to 37.7 °C. Additionally, the hydrolytic solvent cleavage confirmed to have no impact on the PLGA stability. This method presents a significant advancement towards replacing of conventional solvents in the microparticle preparation due to more efficient solvent extraction. 1. Introduction Potentially toxic solvents are needed to dissolve hydrophobic polymers like PLGA or PLA, despite using moderate preparation con- Various pharmaceutical formulations nowadays still rely on the use ditions which are appropriate for sensitive drugs (Bitz and Doelker, of organic solvents. This is particularly true for microparticulate par- 1996). As an alternative, non-toxic solvents could be advantageous enteral formulations intended for controlled drug release of small mo- because they can overcome the safety-related issues. Hence, the use of lecules or protein drugs. The microencapsulation of these substances is non-toxic polymer solvents for multiparticulate systems can be sug- usually based on an emulsification – solvent elimination approach (Ao gested to avoid the issue of a complete residual solvent removal. These et al., 2011; Rosca et al., 2004; Shao et al., 2017). In general, an initial solvents possess a considerable advantage, since they can remain within oil-in-water emulsification step is employed, followed by the elimina- the formulation after preparation of the microparticles due to their low tion of the inner organic phase performed by either extraction or eva- toxicity. Solvents like dimethyl sulfoxide, glycofurol and liquid poly- poration (depending on the vapour pressure of the organic solvent) ethylene glycols have been previously used in this manner (Ali and (Katou et al., 2008; Vay et al., 2012). Lamprecht, 2013; Allhenn and Lamprecht, 2011; Viehof et al., 2013). Different organic solvents are used for the formulation of micro- However, the use of these solvents involves formulation issues such as particulate drug carrier systems (Song et al., 2006). Among the most high viscosity, low drug solubility, potential stability problems, etc. current ones are non-halogented solvents, like ethyl acetate or iso- Previous reports suggested that using ester-type solvents like methyl propanol, but also halogenated solvents like 1,2-dichloromethane. propionate (Kim et al., 2016) and ethyl formate (Sah, 2000), both being However, according to ICH guidelines for residual solvents Q3C(R5), partially water-soluble, can be a good alternative for the production of halogenated solvents possess potential toxic properties belonging to the microparticles, while exhibiting low toxic properties. class II solvents (ICH, 2016). Formulations prepared with class III sol- Here, we propose a new formulation technique based on propylene vents such as acetone or ethanol typically are allowed to contain more carbonate (PC) as an alternative low toxic ester-type organic solvent for “parts per million” residual solvent, but the final removal below the microparticle preparation intended for parenteral administration. PC is permitted threshold after microparticle preparation can be technically a member of cyclic organic carbonates, miscible with most organic challenging (Bitz and Doelker, 1996; Herberger et al., 2003). solvents like acetone, ethanol, chloroform etc. (Fujinaga and Izutsu, ⁎ Corresponding author. E-mail addresses: [email protected] (D. Grizić), [email protected] (A. Lamprecht). https://doi.org/10.1016/j.ijpharm.2018.03.062 Received 12 January 2018; Received in revised form 16 March 2018; Accepted 31 March 2018 Available online 06 April 2018 0378-5173/ © 2018 Elsevier B.V. All rights reserved. ć D. Grizi , A. Lamprecht International Journal of Pharmaceutics 544 (2018) 213–221 1971; Raymond et al., 2009). Also, it is freely miscible with water at 2.2.2. PC hydrolysis tracking concentrations up to 20% (Shaikh and Sivaram, 1996). The ability to The PC hydrolysis tracking was accomplished using thymol blue dissolve a wide range of polymers makes PC an attractive alternative to (TB) as a pH shift indicator which occurs during PC hydrolysis. The commonly used solvents. major analytical drawback for the hydrolysis tracking of PC is the op- However, in the context of alternative safe solvents, plasticization of tical inertness which it exhibits both in UV and VIS region (Fujinaga the polymeric matrix has been identified to be the major issue involved and Izutsu, 1971; Grizić et al., 2016). For this reason, an indirect de- in microparticle design (Jain et al., 2000; Katou et al., 2008; Sah, tection method was employed by using the ability of thymol blue (TB) 1997). This is especially pronounced for water miscible or partially to exhibit pH-dependant color transitions in the regions between miscible solvents like glycofurol or ethyl acetate (Allhenn and pH < 8.0 (yellow) and pH > 9.6 (blue). During PC hydrolysis using Lamprecht, 2011; Sah, 1997). Consequently, solvent-based plasticiza- aqueous sodium hydroxide, ring opening of PC (cyclic ester) occurs, tion is the major hindering factor for microparticle solidification if the which leads to the formation of propylene glycol and sodium hydro- residual solvent quantity is not lowered. gencarbonate. If excess amounts of sodium hydroxide are present, so- In terms of safety considerations, the non-toxicity of PC is under- dium carbonate is formed. For this reason, we evaluated aqueous so- lined in various reports (Beyer et al., 1987; Das et al., 2017; Quintanar- lutions of these potentially forming substances in stoichiometric Guerrero et al., 1996; Sommer et al., 1990). PC undergoes two de- identical concentrations which are formed during the actual micro- gradation pathways either by acid/base-induced hydrolysis (Shaikh and particle preparation using TB and retrieved the respective spectra (Fig. Sivaram, 1996) or enzyme-catalyzed hydrolysis in vivo (Yang et al., S1). The end-point of PC hydrolysis gives a solution with two absorp- 1998). In both cases, cyclic organic carbonates produce carbonic acid tion maxima at 434 nm and 597 nm, respectively. In brief, 5 ml of 2% and 1,2-diols, where the type of the produced diol is dependent on the Na2CO3, 1.5% NaHCO3, 0.15% NaHCO3 and 2% PC were mixed with type of cyclic organic carbonate, confirming the safe degradation of PC 0.05 ml 0.1% ethanolic TB solution and analyzed using a UV–VIS into carbon dioxide and propylene glycol (Clements, 2003). Accord- spectrophotometer (Lambda 12, PerkinElmer UV–Vis spectro- ingly, we were able to enhance the solvent extraction from the poly- photometer, MA, USA), recording their spectra from 400 to 700 nm. meric matrix by the chemical degradation of PC, making PC much more Secondly, the optimal process parameters regarding the hydrolysis of suitable as a polymer solvent compared to non-toxic solvent approaches PC (dropping speed and concentration of sodium hydroxide) which at that have been reported before. the end could affect the stability of the excipients, had to be found. A constant amount of PC (100 mg) and varying concentrations of sodium hydroxide, expressed as the percentage of the maximum stoichiometric 2. Materials and methods amount which is needed for a complete reaction (39.18 mg sodium hydroxide), were used. The analysis was performed using a 1 cm quartz 2.1. Materials cuvette, filled with a mixture of 50 µl 0.1% TB solution and 2 ml 5% PC. Immediately after adding the sodium hydroxide solution, continuous PLGA [Poly(DL-lactide-co-glycolide)] (Resomer® RG 502H) was ob- time-dependent measurements at 434 nm and 597 nm were performed, tained from Boehringer Ingelheim (Germany). Propylene carbonate measuring the absorbance every 2 sec during 30 min. This procedure (PC) was purchased from Merck (Darmstadt, Germany). Glycofurol, was repeated for all sodium hydroxide concentrations. Different con- sodium carbonate, methanesulfonic acid, lactic acid, glycolic acid, so- centrations of sodium hydrogencarbonate (the major product during PC dium hydroxide and hydrochloric acid were obtained from Sigma- hydrolysis) gave different intensities, but always the
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